Catalyst-Free Selective Synthesis of E-Tetrasubstituted Olefins via Tandem Reaction of 3-Acetyl-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione with Amine, C–C Bond Breakage, and Proton Transfer

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

The Z- or E-selective syntheses of tetrasubstituted olefins present big challenges. Tremendous efforts are ongoing to overcome this issue, especially for acyclic structures. In work, an E-stereoselective synthetic method through tandem reaction 1,4-Michael addition 3-acetyl-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione with amine, C-C bond breakage, and proton transfer by intermolecular hydrogen bonds was revealed excellent atom economy without catalysts additives. A diverse set E-tetrasubstituted were obtained in 43% 93% yields functional group tolerance late-stage modifications complex drug molecules. mechanism proposed based on the deuterium-labeling experiment density theory (DFT) calculation.

Language: Английский

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Photoinduced Co-catalyzed dehydrogenative cyclization of 2-alkenylphenyl carbonyl compounds and mechanistic insights

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We present two protocols for the efficient synthesis of substituted 1-naphthols. DFT calculations and verification experiments elucidate mechanism. Scale-up product conversion confirm reaction's practical potential.

Language: Английский

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Intramolecular Dehydrogenative Photocyclization of N-Phenyl-1-naphthamides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5364 - 5369

Published: June 14, 2024

Here, we explore a dehydrogenative 6π photocyclization method for

Language: Английский

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NHPI-Mediated FeTiO₃-Photocatalyzed Semiheterogeneous Decarboxylative Acylarylation of Acrylamides with α-Oxocarboxylic Acids under Nitrogen

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12693 - 12700

Published: Aug. 26, 2024

FeTiO3 has emerged as an interesting semiconductor photocatalyst in organic synthesis. We herein describe a visible-light-induced semiheterogeneous strategy for the synthesis of 3-(2-oxoethyl)indolin-2-ones with moderate to good yields and functional group compatibility using recyclable NHPI redox catalyst.

Language: Английский

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Gold-Mediated Cyclization of N-Acrylamides via Energy Transfer Photocatalysis

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 26, 2024

We disclose a gold-mediated photocyclization method for the efficient synthesis of acrylamide-derived β-lactams and 3,4-dihydroquinolin-2-ones, two privileged bioactive scaffolds. The protocol proceeds with ease, providing good yields product while exhibiting excellent functional group tolerance at low catalyst loadings in sustainable solvents. Additionally, reaction times are significantly reduced compared prior-art methods. Notably, present gold system exhibits superior performance activating poorly conjugated substrates, which typically unreactive other photocatalysts, highlighting exceptional position this organogold among modern photocatalysts.

Language: Английский

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Metal‐free photocyclization/oxidation cascade constructing quinoline‐2‐ones and tetrahydrocarbazolones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4066 - 4072

Published: July 19, 2024

Abstract We reported a one‐pot photocyclization/ oxidation cascade of N ‐aryl acrylamides to afford quinoline‐2‐ones. Thioxanthone was used as bifunctional energy transfer agent mediate both photocyclization and generation singlet oxygen, the latter facilitates dehydrogenation dihydroquinoline‐2‐one intermediate. This strategy also supports 5‐ endo ‐trig cyclization synthesize tetrahydrocarbazolones from phenylamino cyclohexenones.

Language: Английский

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